Jason Creane on Coachability Pt. 1 | Masters of MEDDICC

00:00 Andy Whyte: Hey Jason, welcome to Masters of MEDDICC. It is awesome to have you on the show. For those who don't know you, maybe we could start with you introducing yourself and how you got into this wonderful world of sales. 00:10 Jason Creane: Well, I already feel embarrassed being on a Masters of MEDDICC thing, because I feel like I'm being put on a pedestal — which is definitely not the case. But I'm delighted to be here, to talk to someone so passionate about sales methodologies and good execution. I'm really excited about the conversation. Thanks for that. So how did I get into sales? Well — when do you classify recruitment as sales? Because if you do, the way I got into it was: my dad said to me at the end of university, "Right, you can't go on a gap year unless you've secured a job first. " And I thought, fair enough. So I graduated in 2009 when the financial crisis hit. Getting a job wasn't as easy as I thought it might be. So I went around all the graduate programmes. I ended up interviewing at Ernst & Young, KPMG, and Deloitte. An accountant is the last thing I am — but I needed a way out, right? I needed to get to where I needed to go. I wanted to travel. 00:59 Jason Creane: So I walked in, and I ended up getting only 25% on the accounting exam. No firm would typically hire anyone on 25%. But one of them invited me back. Just one — Ernst & Young. So they said: "Jason, we really liked you in the interview, but we were really surprised you didn't do well on the test. We just wanted to have a conversation to find out what's going on. " And I said to them: "I bet you have lots of people in this business who can do the numbers extremely well. I'm sure there's no shortage of people at Ernst & Young scoring 80% and above on that test — no problem at all. But I bet the thing you don't have in abundance are people who can understand how to interpret those numbers and create stories that convince customers how to change, and what they need to do to improve their businesses where it matters. 01:56 Jason Creane: And I think that's where I could be helpful. I might not have the aptitude around the accounting and the financials — but that's what you have Excel for. I'm sure you don't win clients by just producing perfect audit results. I'm sure you win them by being a brilliant engagement person. " And they said: "OK. " And they gave me the job based on that pitch. I said fabulous. Then I called them back and said: "One thing — I have to defer entry for a year because I want to go travelling. " They reluctantly agreed. Getting to your question now — but I wanted that backstory. I went away to Nepal and lived there for a year, travelling and having a great time. The day I got back, I called Ernst & Young three weeks before I was due to start and said: "I'm really sorry. You've got the wrong guy. I really appreciated you deferring my entry — but I'm not an accountant, and I don't want to pretend to be. " They were not happy. My dad was not happy either. 03:00 Jason Creane: But I never wanted to go into accounting — it was just a means to get the job and leave on my gap year. So instead I ended up starting a recruitment business. And that's how I fell into getting on the phone. 03:16 Andy Whyte: I love it. Brilliant. Can you — actually, you know, in our world, a lot of people in your shoes would have put "EY alumnus" on their LinkedIn profile, even if they never actually started. I know you did technically start — but. 03:16 Jason Creane: I'm more proud of the fact that I didn't go and do something that wasn't right for me. I could have had an Ernst & Young graduate programme contract. Or I could have an £18,000 base salary at a recruitment firm in London where I felt like I could go and make something happen. 03:44 Andy Whyte: Yeah. I love that. And I think our industry is starting to catch on to this. I've seen a lot of things this year in particular that support it. But for a long time, my secret and not-entirely-intentional recruitment channel was former recruiters. If I look back at my greatest hires, I think well over 90% of those who'd make it into my top ten were, at some point, recruiters at the start of what we'd call their sales career. And I think people are starting to catch on. You're a great example of that, given the career you've had. How long were you in recruitment? 04:13 Jason Creane: So I did it for 11 months. I think it was a combination of luck and good timing. A person I worked alongside left and joined Gartner about six months in — her name is Valerie, she now has an amazing career in software sales. She sent me a Facebook message — not LinkedIn, because she was worried about being seen spending all her time on LinkedIn. And I didn't see it for a few months. The message said: "Hey, I heard you on the phone. You were really good. Why don't you come to Gartner and learn the fundamentals of sales? " I got this Facebook message months later and thought: wow, that could be amazing. So I messaged her back, and she referred me into Gartner for an interview. And that's how I got in and out of recruitment. 05:02 Andy Whyte: That's a great place to start a sales career. Gartner is genuinely a fantastic place for the fundamentals. How did you find it? Was there a steep learning curve? 05:28 Jason Creane: Huge learning curve. Because I had loads of self-belief, but very little knowledge at the time. So it was huge self-belief, very little idea about technology. The first six months I didn't sell anything. I joined in August and didn't sell anything for the remainder of the financial year. The year reset at the start of the calendar year. I started to make progress then. And in that year I managed to achieve what they call the Eagle Award — something like the top 1% of performers — and I did that every single year I was there. I don't know exactly why. Maybe we can discuss it. But: first six months, nothing. Then it clicked. And then high achievement from there on. 06:12 Andy Whyte: Interesting. And this thing about clicking — I don't know about you, and I wonder if people listening feel this — but for me I always felt like I was waiting for it to click. Whether I was an individual contributor or a leader, there was always this feeling that one day I'd just wake up and go: "Yep, we're in the groove now. " And even when performances were there and things were running well, the definition of what "clicking" would look like always seemed to move further away. It was always equidistant away. And that was something I never felt comfortable with — even if I could have defined a year earlier exactly what "clicking" would look like, and then actually hit that criteria, I still wouldn't feel like I'd clicked. So when you say it clicked at Gartner — if I asked you in that moment, when you were a top 1% performer, would you have felt like it had truly clicked? Would you still have felt you had a lot more to do? 07:05 Jason Creane: Yes — I would have recognised it at the time. Because with each small success, confidence builds. And then flow starts to build. And when you're in flow, more success comes. As long as you remain consciously competent about the things you're doing well every day that are driving that success, you shouldn't fall off. The risk is: if you're not conscious of what you're doing — if it just feels like magic — it'll probably just be a fluke. You might have a great run, but you won't be able to sustain it. So the secret — as I teach people now in my new role — is to make sure they're working out what is making things work. Because if they don't cement that learning, they won't be able to replicate it and continue. 07:36 Andy Whyte: I love that. And one of the things we always see in our performance industry — because sales is a performance industry, just like sport — is that when you're performing and closing deals, you carry a confidence that leads to you closing more. Because you carry that confidence into meetings, and the customer thinks: this person really believes in what they're selling. They're almost assuming I'm going to buy. So it must be great. And I think that's one element. But there's also this — and I won't get it perfectly right — but it's from Sir Alex Ferguson, probably one of the greatest sports coaches of all time. He talks about strikers and says: when they're scoring, they think they'll never stop. And when they're not scoring, they think they'll never score again. And what you're talking about is brilliant — it's taking that analogy and figuring out what it is about a player's game that's making them score. Making them aware of it so they can keep doing it, and not fall into that rut which we've all been in at some point in our career. 09:56 Jason Creane: Yeah, 100%. In basketball they call it the "hot hand" — where it feels like you just won't stop scoring. The gambler equivalent is thinking they're on an unstoppable run. The difference with the gambler is that every bet is independent — there's no correlation between the last outcome and the next. It's the same with scoring goals: there's no inherent correlation between the last score and the next, unless you consciously understand what's driving it from a skill perspective. So if you close a deal and it goes perfectly well, but you didn't work out exactly why — or if you were just going on gut feeling — you might assume the same will happen next time. But it could equally go the opposite way. 11:02 Andy Whyte: Yeah, exactly. And so when you're working with your team to identify and cement these things — almost building them into their cadence as best practice rather than just gut feeling — how do you identify those moments with your team? 11:02 Jason Creane: So it's actually a huge topic for our leadership team right now, because we're ramping a lot of new people remotely. We have a responsibility to these people to help them get better and become great. They came here to learn. So we have to hold up our end of that bargain and deliver on it. The leadership question then becomes: how do we make sure that actually happens in practice, at all levels of leadership? So we put a huge amount of thought into it — from onboarding through the first 30 days. We have leading indicators about management involvement and specific elements of that process. A best practice around which meetings leadership should attend, which debriefs, which meetings leadership should own, which difficult conversations should be fronted by leadership versus the RSM. All of those elements to make sure we're leading from the front, teaching and showing — so we can cement learning. 13:41 Jason Creane: And then going through almost the slightly awkward process of: "Did you see what I did in that meeting? Can you just talk me through what you observed? Did you notice the way I handled that objection? What did you see that you thought was interesting? " Because we're trying to make sure they're conscious of the things that made the difference — so they can know it was that, in that meeting — versus just "oh, that was a great meeting, I'm not sure what the magic was. " We want to be able to say: "There wasn't magic. It was applying a formula that works, and doing it consistently. "14:19 Andy Whyte: I love that. And people who listen to this podcast will know I relate our industry to sport a lot. And what you're talking about there is essentially reviewing the tape — which we get to do so much better now in the remote world, with tools that can record meetings and play them back. That's what you're talking about doing as a coach — playing back the match video, pointing things out. The positive outcomes from that are brilliant — not just for the individual you're coaching. And this comes back to having that open, collaborative culture. The idea of elevating someone who's done something really well in a meeting and sharing it with the team — that not only gives them recognition for doing something great, it benefits the whole team. And I love what you said about people you've brought in — very high potential people — and that you feel genuinely committed to delivering on your promise to them. That's really cool. 15:27 Jason Creane: We are. And just for the record, we are held to high accountability on that. The default position is: if we hired someone who met our hiring criteria and they're not successful, either we didn't do a very good job assessing whether they actually met the criteria — which shouldn't happen given the layers of assessment we have — or leadership didn't do its job in upskilling that person. Because they came here for the right reasons, and that was validated by several layers of leadership. The only thing that can go wrong after that is if we don't invest the right attention in making them better. And the time lag starts to create a will issue — not learning, not having success, will starts to drop. They start to feel disillusioned. And that's a very hard place to pull someone back from — trying to resell them on the opportunity when their belief is so much lower. 16:15 Andy Whyte: Yeah. And something I've always noticed — I'm sure you've seen this too — is that the very, very best salespeople I've ever worked with, the most elite ones, are always the very first to put their hand up and say when they need help. Whether it's a bad quarter, a deal they think they're going to qualify out of — they're always the very first to say that. And by contrast, for those who don't feel comfortable doing that — in the scenario you described, where someone's not performing — if they're not the type of person who can immediately put their hand up and say "Hey, I don't see myself hitting these numbers. I know I'm capable of what you hired me to do — but something isn't clicking right now" — that is a culture and a dynamic where you can solve the issue much more quickly. Given the thorough hiring process you've described, that's such an interesting dynamic to me. 17:50 Andy Whyte: How do we get people who are earlier in their career to have the attitude of those elite salespeople — who, in theory, should need the least help because they're the most experienced and talented, but are the most comfortable raising their hand? How do we bridge that gap where less experienced but high-potential people can feel like they can be vulnerable? 17:50 Jason Creane: Well — maybe a contrarian point here. I actually find that one of the traits to look for in hiring is comfort with not knowing everything. And I find that younger, less experienced, high-potential people are often the most open to change. They're the most open to saying: "I'm a blank canvas. I want to be just like you. Teach me everything, I have no bad habits, no preconceived ideas, and no ego. " Those people often end up with a much deeper learning curve and greater progression — because of that raw coachability. Versus the contrast: some more experienced people come in thinking they already know what they're doing. They may have a mix of good and bad habits. They may quite rightly have some swagger because they have a track record. So you're going to have to do a much better job convincing them that what you have to say is worth their time. So the learning curve can be more erratic. 19:29 Andy Whyte: But what I love is a slightly different take. The really cool thing about what you just identified is: it's probably not actually correlated with experience level — it's correlated with coachability as a personal attribute. So if you maintain coachability regardless of experience, if it's just your personality and not linked to where you are in your career, then it should remain high regardless. For example — if I'm early in my career and I'm talking to someone like you with a strong track record, I'll naturally be looking up to you and be coachable in your eyes. But am I equally coachable to my peer who's six months or a year ahead of me? That, I think, is a deeply ingrained trait that either runs consistently through a person or it doesn't. 20:34 Jason Creane: And so if I develop two or three decades of top-level sales experience — is my coachability still there? Or does it reduce a little as I look around and think I've already absorbed what most people can teach me? I find that sometimes experience makes coachability less, not more. And so it's so important to keep coachability as high as possible and remain very conscious of it no matter what level you're at. Because otherwise what can happen is — knowledge goes up, coachability goes down. You feel like you know everything, but you're not open to learning. So one line goes to the bottom and the other goes to the top. 21:03 Andy Whyte: Yeah, exactly. And I'll draw that parallel with sport again — the top sportspeople, the ones famous for their work ethic, are the ones coaches say stay late after training. David Beckham — probably in his prime the best free-kick taker in the world — was probably the person taking the most practice free kicks in the world too. And then there's Kobe Bryant and Ronaldo, who are excellent examples of that. The famous Kobe story: one of his teammates decided he was going to be first to practice. To do that, he needed to be at breakfast by a certain time, and then straight to practice. And when he got there, he saw Kobe already there — and thought: "Great, I'm here with Kobe. " But then he noticed Kobe was sweating. He'd already done a full workout. He was already into his second session of the day. And that just blew this player's mind — because Kobe was the best player in the world, and he was getting up earlier and working harder than anyone. And that just encapsulates what that expectation of greatness really means. 22:13 Jason Creane: I love it. Can you imagine that moment — you think you're going to be first, you walk in, and Kobe's already done his work? You're like: "At least I'm second. " And then you realise he's already finished. Phenomenal. And after practice, he'd go to the football pitches adjacent to the training facility and run end-to-end drills across all four. That's the level. And I think this is a really interesting point. Because — to repeat it back to myself, actually — I recently took on a second-line leadership role at the start of the new fiscal year in August. And I think I fell into unconscious incompetence in the new role. I came off the back of a successful first-line management career thinking: I know what I'm doing as a first-line manager, all I've got to do is teach other people to do it. Logic sort of adds up, right? 23:34 Jason Creane: What's turned out to be such a different type of job — much more about identifying themes and metrics and data points that indicate where problems might be emerging, creating enablement that's broad and scalable, thinking about how people are feeling as a coach — all of this stuff wasn't really relevant when you were so deal-focused as a first-line manager. And I've gone through a few lightbulb moments in just the last month or two where I thought: I was unconsciously incompetent in my new role. I almost became the person with experience who wasn't being vulnerable — but some of those experiences have since made me realise: this needs to dial back up again. And it gives you a really stark reminder that you haven't got it all figured out yet. Mistakes and problems are a really good reminder of that. 24:23 Andy Whyte: Yeah. And I think that's actually really interesting. When I look at your career and listen to some of the things you've spoken about, I think there's a correlation here — bear with me. You stepping into that new role — it's almost like you didn't know what you didn't know. And so that gap between where you were and what you needed to step up to — you couldn't be coachable on it, because you weren't aware it existed. But what I found interesting about the way you described it is: you recognised that gap quite quickly. You reflected on it, set higher expectations of yourself, and started working towards meeting those. That is actually a coachable trait. The un-coachable version of that scenario would have been to go into the role, not see the gaps, and not see the opportunity to learn — because you were being exposed to genuinely new things. So I think that points back to something that stood out for me: you were a top performer at a great company like Gartner. Top 1%. At some point, I think, even globally. 25:41 Jason Creane: Yeah. 25:41 Andy Whyte: So why on earth would you not be someone who stays at Gartner for their entire career? 26:23 Jason Creane: I've spoken about this before, but I think it goes deeper than it first sounds — and I mean no disrespect to Gartner, which is an amazing company. But I just felt like whenever I looked around, I didn't see anyone I really admired and wanted to become. When you're faced with the prospect of growing up inside that company, it's almost like it can't happen. Because no matter who you meet at any level, you're thinking: I don't see myself as that person. I don't feel a desire to be like you. And if I'm having this conversation with someone like me in 20 years' time, I don't think I'll feel very fulfilled. That makes you feel like you've got to leave. There's this urgency — like fight or flight when something's wrong. It becomes quite immediate. You've already made the decision. All that's left is to act on it. And that's what I did. 27:23 Andy Whyte: Yeah. And what I find interesting — taking an abstract view of what you're describing — is that you kind of mentored yourself through Gartner. It was a steep learning curve, so you weren't landing there already knowing what you were doing. You levelled up. And this is something I don't think we talk about enough in our industry: you were identifying the ceiling of your own potential within Gartner. And in sales in particular, we constantly compare ourselves to others around us — which is fine, to a point. We compare ourselves to our team, to people in our network, to peers in other regions. And we draw parallels between our performance and theirs. We might look at people we started out with and compare where we are now — and that can tell us something about whether we're meeting our potential. But I also think something we don't talk about enough is how we have an innate, internal sense of what our own potential is. And the real question is whether we're measuring ourselves against that. 28:53 Andy Whyte: I describe this as something I've felt myself — and this is funny, not to make it about MEDDIC, but before I learned MEDDIC, I would always describe myself as a B-player version of myself. Forget anyone else. I was a B-player by my own standard. Using a sports analogy: I was a player who could use both feet but was only using my right. And then somebody told me I could use my left foot too. And all of a sudden my game improved dramatically. And I think what I see — particularly with very high-potential, talented people in our industry — is that they just can't settle. That's why people keep climbing. The people in sales management aren't always the highest-paid — it's not a role people typically take for a pay rise. What I often see is people moving into more senior roles or into leadership because they're constantly striving to meet their own potential. And what you described at Gartner sounds exactly like a glass ceiling — you could see the full potential of yourself, but you couldn't reach it from inside Gartner. Does that resonate? And if so — how did you take that feeling and do something positive with it? 30:36 Jason Creane: Very interesting. I really enjoyed hearing that. It's funny you talk about achieving your full potential, because someone was asking me recently about my sense of purpose — what motivates me. And one of the things I said was this almost uncomfortable desire to achieve my full potential. My partner Lucy — when she chose to partner with me in life — always told me she thought I could achieve anything I wanted. She's like a cheerleader. And achieving my full potential isn't only about me. It's almost like it's for her too. If I chicken out, if I don't do it, I'm somehow not living up to the promise she saw in me. And it's an uncomfortable feeling — to fall short of someone's expectations of you. Of what they believed you could be. To have had the character, the intelligence, the ability, the drive, the focus, the discipline — and still fallen short. That's a horrible feeling to recognise. 32:34 Andy Whyte: Yeah. I think what it sounds like you're saying is that Lucy is your accountability partner. She's obviously much more than that — but she's your accountability partner. She becomes an outlet that makes it about more than just your own accountability to yourself. And that subconsciously or consciously drives you forward more consistently towards your goal — which is always meeting your potential. Because otherwise you carry this weight, as you described at Gartner. You feel like you're not meeting your full potential. And you owe that to yourself because that's just how you're wired. You can't help it. You can't train yourself out of it because you're always aiming for the next thing. And what Lucy becomes is your accountability partner — which just makes it slightly more like a team effort towards a shared goal. 33:20 Jason Creane: I agree. And it doesn't limit itself to professional life. An accountability partner should be testing you on becoming the best version of yourself as a person overall — and calling you out when they feel like you're not meeting that bar of expectation. That makes you continue to evolve and live within your relationship in a culture of constant improvement and growth — as people, as parents, as individuals, as financial planners, as professionals, as partners, as role models. You continually evaluate your own potential across all of those areas. And that's why I think I can now relate to — I don't mean this how it sounds — when someone's at the Oscars giving that acceptance speech and they say: "I want to thank my partner for everything they've done. " That always used to sound clichéd to me. But actually that person probably held them to account for everything they achieved in their life. 34:35 Andy Whyte: Yeah, I love that. And that does it for me — whether it's a partner in a relationship, or parents — parents are probably your first cheerleaders. The ones who see your full potential, maybe even more than you do. If I think about my mum — one of her near-catchphrases is that I've "missed my vocation in life. " I could give one of my kids a terrible haircut in lockdown and my mum would say: "Oh, it's brilliant — you should have been a barber. " So yes. Anyway — what did you do? You were at Gartner, crushing it, but you knew you needed to take yourself further. How did you fix that? 36:38 Jason Creane: So I think I've been blessed with some good fortune. What happened was: I got introduced to Steve McCluskey — and that was the first meeting I had once I'd made the decision to leave Gartner. And that's a pretty remarkable first meeting to have, with a really exceptional company and person of excellence. So there was a bit of good fortune in that. I didn't go and create an amazing plan, a long list of target companies. I just got the good fortune of meeting someone exceptional. And to paint the contrast from why I wanted to leave — it was the absence of people I admired. As soon as I met Steve, he made me feel uncomfortable. He made me feel out of my depth, like a bit of a fool, like he could see right through me. 37:23 Jason Creane: I arrived in a really sharp suit, as if I'd already made it. I walked in casually, didn't even bring a notepad — kind of going for a peer-to-peer conversation. And I think he gave me the benefit of the doubt. He's seen a lot of people like me: potential, smart, a lot of guts — but he knew exactly where I was in my development. And he didn't choose to use that as an opportunity to tear me apart. Instead, slowly but surely, he helped me realise how out of my depth I was — through questioning. Just putting the onus on me to control the meeting. But I was unable to do so. I was watching myself flounder, unable to find a route through. And he was like: "OK, so you see what's happening? You see the skills you're not demonstrating? Do you see how I could help you? " And I was like: "Oh my God. " That was another realisation. The urgency had shifted. Before it was about deciding I needed to leave Gartner — that had been decided. Now I didn't care about the company, didn't care about the prospects of the business, didn't care about any of that. 38:40 Jason Creane: I just met an individual I thought I could learn a hell of a lot more from than from anyone I was learning from at that point. Nothing else mattered. It was just: Steve, because you've just demonstrated in this moment that I could learn a hell of a lot from you — that's the only reason I'm changing what I'm doing. So bring it on. 39:17 Andy Whyte: You know why I was smiling so much when you were telling me that? Steve was implicating you in the pain of your situation. And he eradicated everything else. If you think about that in a sales context — because that's effectively what he did — I'm sure if we spoke to Steve, he'd remember, as we all do, the people we hired who went on to be hugely successful. And I think what he was doing at that point was selling you — even though it was still technically part of a qualification process. He was qualifying whether you had the coachability. In this scenario: raw talent, yes. Frameworks, not yet. And so he probably spotted you as a top Gartner performer and knew why you were there. And he was making you feel like there was nothing else in the world that mattered more than getting this job. 40:00 Andy Whyte: Because that was the only thing that was going to help you reach your potential. And what did you do? I could feel it. I could feel it as you were telling that story — even though it was seven or eight years ago. You could feel the pain you were in in that moment of seeing your own potential right there in front of you. 40:17 Jason Creane: Yeah, yeah. I was feeling two things. One was: "Oh my God. I can't let this slip away. " Oh my God, I need to convince him that I'm good enough for this job. Because if I don't — if I don't get in — my life is over. Everything is going to fall apart. I had that single-mindedness. I had to do everything I could to get this job. And the second thing I felt was: what a contrast between the way I walked in and the way I'm walking out of this meeting. I walked in with swagger. I'm walking out with humility. And I hadn't felt that kind of freedom — that reset — in quite some time. It was a good reminder, like the one I just described in my new role: you get these moments of humility. "Oh God, I really didn't recognise that in myself. And I now need to choose to embrace it. " It's uncomfortable. I don't love looking at it in the mirror. But I'm up for it — because I have to achieve my full potential. So let's get back on the horse and get going. 41:43 Andy Whyte: Yeah. I'm still smiling at everything you just described — because if you could ever get your customer in that same moment of pain about the prospect of not buying your solution, that is what drives urgency. You said it yourself without even framing it in a sales context: you were urgently wanting to work for Steve in that moment. And the interesting thing — correct me if I'm wrong — but the company you joined wasn't quite the company we know it as today, was it? It was, I think, right at the point before a significant acquisition, in that period where —